Enterprise Sales Development Representative - Retail

Lightspeed Commerce; Toronto; Hybrid; CAD 70,000 - 90,000; Full time

Job summary

A dynamic technology company in Toronto is looking for an Enterprise Outbound Sales Development Representative to drive revenue by generating leads for enterprise retail clients. You will proactively engage with enterprise stakeholders, collaborate with Account Executives, and achieve outbound sales goals in a fast-paced environment. Ideal candidates will have 2-5 years of SaaS outbound sales experience and strong communication skills. Join a culture that values your growth and contributions.

Benefits

Flexible paid time off

Equity options

Pension plan contributions

Training opportunities

Health and wellness credit

Volunteer time off

Computer purchase program

Enhanced parental leave

Qualifications

• 2–5 years of experience in SaaS outbound sales with enterprise clients.
• Proven experience in engaging enterprise stakeholders.
• Strong communication skills to convey complex solutions.

Responsibilities

• Prospecting enterprise retail accounts through various channels.
• Building relationships with enterprise-level stakeholders.
• Collaborating with Account Executives for strategic follow-up.

Skills

SaaS outbound sales

Cold calling

Relationship building

Strategic thinking

Fluency in English

Job description

Hi there! Thanks for stopping by 👋

Are you actively looking for a new opportunity? Or just checking the market? Well… you might just be in the right place!

Lightspeed is looking for a highly motivated Enterprise Outbound Sales Development Representative to join our North American Outbound Sales team. You’ll help drive revenue growth by generating and qualifying leads for enterprise retail clients, acting as the first point of contact and helping empower retailers.

Our Enterprise Outbound team is in hyper‑growth mode, and we need a driven, strategic, and energetic individual who is passionate about helping larger retail businesses grow. If you’re results‑driven and excited to join a fast‑growing company, this is the role for you.

What you’ll be doing:

• Proactively prospecting enterprise retail accounts via phone, email, social media, and other outbound channels.
• Reaching out to enterprise‑level stakeholders (Directors and above) to understand their challenges and build strong relationships.
• Collaborating with Enterprise Account Executives to ensure smooth lead handoff and strategic follow‑up.
• Providing feedback to marketing and sales teams based on prospect conversations to help refine outbound strategies.
• Consistently achieving monthly, quarterly, and annual outbound sales goals in a high‑velocity environment.

What you’ll be bringing:

• 2–5 years of experience in SaaS outbound sales, preferably with enterprise or mid‑market retail clients.
• Proven ability to cold‑call, email, and engage enterprise stakeholders in complex sales cycles.
• Strong communication and relationship‑building skills, with the ability to explain complex solutions to multiple stakeholders.
• Tech‑savvy, strategic, and comfortable navigating enterprise accounts.
• Entrepreneurial mindset, bias toward action, and the ability to adapt quickly in a fast‑growing business.
• As a global company with employees and clients outside of Quebec, fluency in English as a working language is required for this position.

Even better if you have:

• Experience selling into enterprise retail clients.
• Familiarity with POS systems or other software platforms in large organizations.
• Experience with consultative selling approaches such as MEDDPICC or BANT.

What’s in it for you?

• A flexible work environment that empowers you to do your best work
• A culture that celebrates performance
• The chance to make an impact in a team that’s big enough for career growth, but lean enough to make your voice heard
• Career‑defining opportunities

Benefits

• Flexible paid time off and remote work policies
• Equity options, because this is your company too
• Contributions to your pension plan. Your future matters
• Training opportunities to grow your skills and career
• Health and wellness credit so you feel your best
• Time off to volunteer and give back to your community
• Interest groups, employee led networks, social committees to sponsored sports teams
• Computer purchase program to get your personal Macbook
• Enhanced parental leave to support growing families

Fuel your growth. Find your people.

At Lightspeed, your growth is our priority. We invest in you with continuous learning opportunities, global mobility and benefits designed to support you—all within a driven, diverse and inclusive team that’s passionate about empowering our communities.

To all recruitment agencies: Lightspeed does not accept unsolicited agency resumes. If we have not directly engaged your company in writing to supply candidates for a specific vacancy, Lightspeed will not be responsible for any fees related to unsolicited resumes.

Lightspeed is a proud equal opportunity employer and we are committed to creating an inclusive and barrier‑free workplace. Lightspeed welcomes and encourages applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of this selection process.